How to successfully navigate all of life’s milestones

This site and certain third parties would like to set cookies and access and collect data to provide you with personalized content and advertisements.

If you would like this personalized experience, simply click accept. If you would like to opt-out of this data collection, please click "decline" to continue without personalization.

Maaaan, life is hard. It's so unpredictable.

Just when you think you have it figured out, you're thrown a curveball and whiff. Badly.

In baseball, you get more at-bats. You start seeing more curveballs and you get better at hitting them.

Life isn't that much different. What if I told you it's not that unpredictable. It only looks unpredictable.

Many of life's problems already have solutions. What worked three hundred years ago, often still works today. The tools might be slightly different and the situations might be slightly different, but they're pretty much the same. The ball might curve a little differently but, fundamentally, a curve is a curve.

That's why you see all those “things I should've done in my 20s” or “why millennials are…” articles. One of the tricky things about writing for an audience greater than one is that you are often pushed to make generalizations. We see it all the time in mainstream media. (oh and those “Generation whatever is the reason we're all in some kind of mess — just throw those in the trash)

Despite the passing years, many of our challenges remain the same. How do I get a job? How do I find a mate or get my family off my back about not wanting a mate? How will I get a raise? How will I retire? How will I start a family or get my own family off my back about not wanting to start a family?

As individuals, it's more effective to think in life cycles and milestones, not in ages or generational cohorts (GenX, Millenials, GenY, blah blah).

There are a handful of milestones that most people will experience – marriage, divorce, starting a family, first job, getting fired, second job, retirement, death, etc.

Not everyone will experience every life event but at each major milestone, you and your thinking will shift a little. You need to draw more knowledge from someone who has navigated the event already, less from someone who happens to be closer in age. That's how you overcome those challenges successfully.

If you want to successfully navigate all of life's milestones, the answer isn't in asking people your own age or reading articles for people your own age.

On average, a 30-year-old woman who is expecting a child will have more to learn from a 45-year-old woman with kids than another 30 year old who isn't expecting or have kids. It could be on big issues, like “how do you balance kids versus career?,” or small ones, like “what do for childcare during teacher in-service days?”

The 15 year age difference is less significant than the milestone of having and raising children.

The different “generations,” which are themselves artificially created anyway, are even less important. The 30-year-old will face the same issues the 40-year-old may have faced and will draw inspiration and knowledge from her.

When you have a problem, do you look to someone in your generation?

Or to someone who has faced those issues before?

If you're wise, the latter. 🙂

The internet is fantastic for this type of research because people are sharing their experiences every single day. If you have an interview with Google, Microsoft, and Amazon – you can search through hundreds of stories to get a better idea of what to expect.

If you're just looking for an internship or looking for better mental models of how to get a job, you can find hundreds of experts who have distilled their experiences working with thousands of individuals. Through one person you can get the best of the best from the experiences of thousands — how awesome is that? It's freaking unbelievable. (if this describes you, you need to read Ramit Sethi's Briefcase Technique AND his Truffle Principle — it will fundamentally change your mental models about hiring)

Remember, all this has happened before, and all of it will happen again. Don't make other people's mistakes twice. 🙂

After I wrote this post, I stumbled onto an episode of Hidden Brain in which Shankar Vedantam and Dan Gilbert talk about how we're horrible at predicting the future. One of the solutions is to ask someone who has already experienced something to share their impressions, like about a movie or a date. This is exactly what I mean about speaking to someone who “navigated the event already,” vs. someone closer in age.